I’m booked BER-ZRH-ORD next month. The first leg is economy on LX, and the second is PP on UA. I’m currently waitlisted for a mileage upgrade, but it occurred to me that for the right price (say, under $1000) I’d be happy to just pay for the upgrade. Is it a better plan to cancel the upgrade request and keep checking the price, then re-request the mileage upgrade say 5 days before the flight if the price doesn’t materialize? Or just keep the current request and hope?

I’m UA Gold too.